Acetic Acid → Methyl (Z)-3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-(carboxymethoxy)propenoate

HRID 362284

反応式

HRID 362284 の反応式
[H-].[Na+].[C:3]([O:12]C)(=[O:11])[CH2:4][O:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[N:23]([CH2:25][CH2:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)[CH3:24].C(O)(=O)C>C1C=CC=CC=1.O>[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[N:23]([CH2:25][CH2:26][O:27][C:28]1[CH:35]=[CH:34][C:31](/[CH:32]=[C:6](\[O:5][CH2:4][C:3]([OH:12])=[O:11])/[C:7]([O:9][CH3:10])=[O:8])=[CH:30][CH:29]=1)[CH3:24]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 2018771,1'-Dimethyl 2,2'-oxybis(acetate)HCID 100402134-[2-(N-Methyl-N-(2-benzoxazolyl)amino)ethoxy]benzaldehyde

生成物 1

HCID 86753267Methyl (Z)-3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-(carboxymethoxy)propenoate

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

実験手順

A mixture of sodium hydride (60% dispersion in mineral oil. 0.30 g), dimethyl diglycolate (0.81 g) and 4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]benzaldehyde (2.22 g) in dry benzene (50 mL) was stirred at room temperature overnight. Acetic acid (1 mL) was added, the mixture was poured onto iced water and extracted with ethyl acetate. The combined ethyl acetate layers were washed with water, dried (MgSO4) and evaporated. The resulting oil was chromatographed on silica gel using 2% methanol in dichloromethane, and the product crystallised from ethyl acetate, mp 111°-112° C.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined ethyl acetate layers were washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe resulting oil was chromatographed on silica gel using 2% methanol in dichloromethane
  6. customthe product crystallised from ethyl acetate, mp 111°-112° C.

出典と根拠

ORDレコード
ord-349088323bb042b2b50b80f050556ffa
出典データセット
uspto-grants-1999_02
特許番号
US05869495

関連ノート

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